GB751723A - Processes and intermediates for the production of synthetic androgens from coniferous resin acids - Google Patents

Processes and intermediates for the production of synthetic androgens from coniferous resin acids

Info

Publication number
GB751723A
GB751723A GB27338/51A GB2733851A GB751723A GB 751723 A GB751723 A GB 751723A GB 27338/51 A GB27338/51 A GB 27338/51A GB 2733851 A GB2733851 A GB 2733851A GB 751723 A GB751723 A GB 751723A
Authority
GB
United Kingdom
Prior art keywords
compound
halide
unsaturation
derivative
carbinol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB27338/51A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NICHOLAS THOMAS FARINACCI
Original Assignee
NICHOLAS THOMAS FARINACCI
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by NICHOLAS THOMAS FARINACCI filed Critical NICHOLAS THOMAS FARINACCI
Publication of GB751723A publication Critical patent/GB751723A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/88—Unsaturated compounds containing keto groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
    • C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises polyhydrophenanthrones having the formula <FORM:0751723/IV(a)/1> wherein q represents the group -COCH3, with C ring unsaturation in the (1,2) position, or q represents the group <FORM:0751723/IV(a)/2> or <FORM:0751723/IV(a)/3> with C ring nuclear unsaturation in the (11,1) position, and polyhydronaphthone propionic derivatives having the formul <FORM:0751723/IV(a)/4> and <FORM:0751723/IV(a)/5> where q represents the group -COCH3 with nuclear unsaturation in the (3,4) position, or <FORM:0751723/IV(a)/6> or <FORM:0751723/IV(a)/7> with nuclear unsaturation in the (4,10) position, and the production of compound I by heating a nuclearly mono-unsaturated ester derivative of d-pimaric, abietic, neoabietic or laevopimaric acid having the formula <FORM:0751723/IV(a)/8> wherein m represents -CH(CH3)2, <FORM:0751723/IV(a)/9> or <FORM:0751723/IV(a)/100> and R represents an alkyl or aryl residue, with a mixture of a phenyl magnesium halide and an organic solvent to form a tertiary diphenyl carbinol, reacting said tertiary diphenyl carbinol with a halogenating or hydrohalogenating agent to form a carbinol halide <FORM:0751723/IV(a)/111> wherein m represents H, halogen or methyl, p and t represent H or halogen and n represents -CH(CH2)2, -CH=CH2, -CHOHCH2OH, -CHOHCH3, or COOH, effecting re-arrangement-dehydration of said carbinol halide by means of a dehydrating agent to form an anhydro-halide derivative, oxidizing said anhydro derivative by means of a hexavalent chromium compound at a temperature in the range 20 DEG to 70 DEG C. to form a polyhydrophenanthrone halide <FORM:0751723/IV(a)/122> and reacting said polyhydrophenanthrone derivative with a dehalogenating or dehydrohalogenating agent to produce compound I. Alternatively the compound VII after treatment with a dehydrating agent to produce an anhydro-halide, is heated with a hexavalent chromium compound at a temperature greater than 70 DEG C. to form a compound having the formula <FORM:0751723/IV(a)/133> or <FORM:0751723/IV(a)/144> which after heating with a dehalogenating or dehydrohalogenating agent form the compounds (Ia) or (Ib). As starting materials there may be used abietic, laevo-pimaric, neoabietic and dextro-pimaric acids. The grignardisation step may be effected between 40 DEG to 100 DEG C. in an organic solvent, e.g. benzene, toluene or butyl ether. Oxidation may be effected with chromium trioxide, a bichromate, chromate or chromyl compound, preferably in the presence of an ortho-phosphate producing compound such as orthophosphoric, pyrophosphoric, metaphosphoric acids and anhydrides thereof. As dehydrating agent there may be used P2O5, acetic anhydride, sulphuric acid or toluene. Dehalogenation may be effected with zinc-acetic acid and dehydrohalogenation with pyridine mixture. Examples describe the production of the compounds V, VII, XI, XIII, XV, XVII, I, Ia and Ib. Specifications 751,830 and 751,831 are referred to.
GB27338/51A 1950-12-02 1951-11-21 Processes and intermediates for the production of synthetic androgens from coniferous resin acids Expired GB751723A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US751723XA 1950-12-02 1950-12-02

Publications (1)

Publication Number Publication Date
GB751723A true GB751723A (en) 1956-07-04

Family

ID=22124025

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27338/51A Expired GB751723A (en) 1950-12-02 1951-11-21 Processes and intermediates for the production of synthetic androgens from coniferous resin acids

Country Status (1)

Country Link
GB (1) GB751723A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2894958A (en) * 1957-02-21 1959-07-14 Hoffmann La Roche 2-acetyl-7-oxo - 1,2,3,4,4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene and process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2894958A (en) * 1957-02-21 1959-07-14 Hoffmann La Roche 2-acetyl-7-oxo - 1,2,3,4,4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene and process

Similar Documents

Publication Publication Date Title
GB751723A (en) Processes and intermediates for the production of synthetic androgens from coniferous resin acids
GB929279A (en) Steroids and their production
FOX SYNTHETIC TUBERCULOSTATS. II. AMINO-AND HYDROXY-PYRIDINE CARBOXYLIC ACID DERIVATIVES
GB751831A (en) Processes and intermediates for the production of synthetic androgens from coniferous resin acids ii
US3808232A (en) Process of preparing 4-halomethyl coumarins and compounds
GB751830A (en) Processes and intermediates for the production of synthetic androgens from coniferous resin acids iii
Birch et al. 159. Oxidation of [2: 2: 1] bicyclo heptene-2 (norbornylene)
Hauteville et al. Novel synthesis of dianthalexin (phytoalexin) analogues preparation
GB629177A (en) Manufacture of new hydrazine compounds and derivatives thereof
GB714938A (en) Process for the preparation of tetrahydro-fluorenone
HUT40995A (en) Process for producing esters of 4-/acyloxy/-3-oxo-butiric acid
US2702807A (en) New class of halo-phthalides and methods of preparing the same
US3357992A (en) Process for preparing sultones
GB685133A (en) Aryl-trichloroethanols and their manufacture
GB1399184A (en) Substituted quinolinecarboxylic acids
GB666713A (en) Manufacture of new spirans
JPS55149253A (en) Maleimido and its preparation
Weis Meerwein arylation reactions of olefins with anthraquinone diazonium hydrogen sulfates: formation f new carbon bonds at the carbon atoms C-1 and at C-1
US2678931A (en) Disubstituted octahydronaphthalene-1, 2-dicarboxylic acid
GB613648A (en) Manufacture of organic silicon compounds
GB630860A (en) Process for the preparation of nuclear substituted quinoline compounds and intermediates therefor
KISHIDA et al. The Addition Reaction of Diethyl Acetamidomalonate Anion to Ethyl α, β-Dibromoacrylate, and the Base-catalyzed Reactions of the Adduct
DK157754C (en) METHOD FOR PREPARING 4-METHYL-5-OXO-3-THIOXOTETRAHYDRO-1,2,4- (2H, 4H) -TRIAZINES
US1938053A (en) Hydroxy-thionaphthene compound
GB738766A (en) Production of 20-ketopregnanes